I recently read an analogy that Robert Scobble used to describe why Microsoft failed to jump on the Web 2.0 bandwagon back in 2004-05 when things were starting to heat up.  I'm stealing the premise here to ask a slightly different question (he probably stole it from somewhere else anyway).

 

So the question is, which would you rather have... a penny that doubles it's value every day for 30 days or $100,000?  Obviously, if you do the math, your penny would end up being worth over 100x as much, but not until far into its cycle (see below):

 

 

So perhaps the choice is obvious, but let's put some real world variables into the scenario.  What if there was an increasing chance each day that your penny would stop doubling... maybe this starts low, but by, say day 23 it was at 50%?  Or what if each day represented a larger timescale... perhaps day 30 was the last day of your life?

 

Think about how you make opportunity risk decisions- what other factors or variables might weigh into your decision? [stop reading for a second and think about the last question]

 

If we could ever know all of these variables we could just analyze each one and make the most sensible decisions, but this is rarely the case and so most of us have developed part of our personality to make these decisions from an emotional or gut level.  If you believe Malcolm Gladwell's book Blink we might be much better at this than we think.

 

*I* think by understanding our own personalities in these ways we can actually be content in life, free from regrets, and believing that we truly want what we have instead of always wishing we had what we want.  Then again, I'm a pretty optomistic person that also has written about failing fast, the journey of learning, and the importance of being wrong occasionally.